The Preparation of α‐Alkylidene‐γ‐Butyrolactones Using a Telescoped Intramolecular Michael/Olefination (TIMO) Sequence: Synthesis of (+)‐Paeonilactone B | Zendy

Edwards Michael G. | Zendy; Kenworthy Martin N. | Zendy; Kitson Russell R. A. | Zendy; Perry Alexis | Zendy; Scott Mark S. | Zendy; Whitwood Adrian C. | Zendy; Taylor Richard J. K. | Zendy

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The Preparation of α‐Alkylidene‐γ‐Butyrolactones Using a Telescoped Intramolecular Michael/Olefination (TIMO) Sequence: Synthesis of (+)‐Paeonilactone B

Author(s) -

Edwards Michael G.,

Kenworthy Martin N.,

Kitson Russell R. A.,

Perry Alexis,

Scott Mark S.,

Whitwood Adrian C.,

Taylor Richard J. K.

Publication year - 2008

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200800558

Subject(s) - intramolecular force , chemistry , sequence (biology) , michael reaction , stereochemistry , natural product , organic chemistry , catalysis , biochemistry

A novel telescoped intramolecular Michael addition/proton transfer/HWE olefination sequence has been developed to provide rapid access to α‐alkylidene‐γ‐butyrolactones. This methodology has been applied to prepare a range of tetrahydrobenzofuran‐2,5‐diones, and related systems, and also utilised in an extremely short synthesis of the natural product (+)‐paeonilactone B in enantiomerically pure form. In addition, preliminary experiments are described that illustrate a palladium‐catalysed variant proceeding by way of a π‐allyl intermediate. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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